Al Capone gangster tour of Chicago

1920s Chicago: a city fuelled by crime, lawlessness, alcohol, and the strains of wild jazz music. Today, you can take in the history of Chicago's seedy past with an Untouchable Gangster Tour.

History Facts

Where: Chicago, Illinois, Midwest USA
When: 1920s
History: Lawless ground of violent crime, shootings, and gang warfare run by the notorious Al Capone
Best sights: St. Valentine’s Massacre site, Capone’s moonshine brewery and spot where John Dillinger met his match to the FBI

1920s Chicago: a city fuelled by crime, lawlessness, alcohol, and the strains of wild jazz music. In January 1920, the Volstead Act was made a national statute, prohibiting the consumption of alcohol everywhere. Instead of inspiring the civic obedience its pious enforcers envisaged, Prohibition increased crime greatly by igniting the bootlegging moonshine and beer wars fought by the Chicago gangs. The biggest and most notorious gangster of them all was Al Capone.

Who was Al Capone

Capone was born in Brooklyn, New York in 1899 into a rough neighbourhood. At school he joined two gangs: the Brooklyn Rippers and the Forty Thieves Juniors. He quit school at fourteen to dedicate most of his adult life to the criminal fraternity, joining the Five Points gang in Manhattan, and working as a barman and bouncer in gangster Frankie Yale’s Harvard Inn. Here he received the wounds that gave him the nickname “Scarface“.

After killing two rival gang members in New York, he arrived in Chicago in 1919 to let things back in New York cool down and set up home at 7244 South Prairie Avenue. In Chicago he became the protégé of gangster John Torrio, becoming his business partner after just three years and taking over the racket when Torrio was run out of town. Capone ruled the city’s illegal vice network – comprising of brothels, speakeasies, gambling halls, race tracks, breweries, and nightclubs – between 1925 and 1930. His underground empire was rumoured to have netted an income of $100 million per year. He was run out of town to Florida in 1928. Capone was eventually caught by a bunch of determined Federal Agents, known as the ‘Untouchables‘, led byEliott Ness, who procured to convict Capone on a simple charge of tax evasion in 1931. He died of syphilis in Miami, Florida in 1947.

Take a Gangster Tour of Chicago

Today, you can take in the history of Chicago’s seedy past with an Untouchable Gangster Tour. The tours, which run every day and take two hours, are led by guides wearing gangster suits and talking the lingo. For $24 you’ll be ushered on board an old school bus that’s been painted black to make it look like an old gangster car. The guides are funny but also extremely knowledgeable. You can take in the sights like Cicero Restaurant where Capone had a speakeasy; Al Capone’s brewery; Holy Name Cathedral, site of an assassination; Chinatown – Capone’s area with the church where he prayed, his first place of work, and where he first shot a gangster; the Sicilian neighbourhood, and the site of the St. Valentine Day’s Massacre.

Top Gangsta Sites in Chicago

St. Valentine’s Massacre Garage

2122 N. Clark Street is the site of Capone’s most notorious killing. On February 14th 1929, four of Capone’s men, two dressed as police, went into a garage which was the liquor headquarters of rival “Bugs” Moran’s North Side gang. Moran’s men, thinking it was a police raid, dropped their guns and put their hands against the wall. Capone’s gang leaded them with 150 bullets killing seven men, though Moran was in safety across the road. Capone had a watertight alibi – he was in Florida that day. City officials – reluctant to celebrate their dark past – have removed all signs of the garage’s existence and today the site is a fenced garden.

Shoenberg Brewery

The Shoenberg Brewery is a magnificent old, brownstone building. In 1927 there were 30,000 ‘speakeasies‘ (so called from ‘speaking easy’ so that cops couldn’t hear) in the United States – twice the number of legal bars before the era of prohibition. Shoenberg was where Capone’s gang stored and brewed liquor to supply to the speakeasy racket.

Red Lion Pub

Chicago’s other 1930s outlaw was John Dillinger, notorious bank robber, murderer, and the nation’s public enemy number one – according to the FBI at the time. Every year in July, curious anoraks assemble to commemorate the death of this alternative folk hero outside the Biograph Theatre where he was betrayed to FBI agents by Romanian brothel-keeper Anna Sage. The agents took their cue to shoot Dillinger on spotting Anna’s striking red dress as she led him out of the cinema at 10.30pm on July 22nd 1934. During the commemoration, a procession leads to the very spot where Anna Sage and her girlfriend, Polly Hamilton, accompany an oblivious John Dillinger out of the cinema that fateful night. The event is replayed and re-enacted accurately, including the match lit by Special Agent Melvin Purvis which alerted fellow agents of the outlaw’s exit. The event’s highlight is the ritualistic pouring of beer over the exact spot Dillinger fell to the FBI’s bullets.

More Information

Tommy Gun’s Garage Although prohibition has long gone, it hasn’t been forgotten. A great way to relive the experience is to visit the Tommy Gun’s Garage, at 2114 S. Wabash in Chicago, a gangster and flappers revue. You’ll have to give the secret password to get it, there’s a police raid in the middle of the show, and you can dance the Charleston, 20s style.